Lithium (1-Hexynyl)(2-tri-n-butylstannylvinyl)cuprate

[91158-78-0]  · C20H38CuLiSn  · Lithium (1-Hexynyl)(2-tri-n-butylstannylvinyl)cuprate  · (MW 467.78)

(mixed organocuprate; introduces vinylstannane group)

Preparative Methods: prepared in situ from 1-Hexynylcopper(I) and (E)-1-Lithio-2-tributylstannylethylene.1

Handling, Storage, and Precautions: air and moisture sensitive; use in a fume hood.

Lithium (1-hexynyl)(2-tri-n-butylstannylvinyl)cuprate (1) provided a trans ethylene dianion equivalent in the total synthesis of pleraplysillin-I. Addition of (1) to 3-furfuryl bromide (2) gave the furanylstannane (3). Palladium-catalyzed coupling of (3) with triflate (4) in the presence of Lithium Chloride provided pleraplysillin-I in two steps with complete retention of the trans alkene stereochemistry (eq 1).

Related Reagents.

1-Hexynylcopper(I); Lithium (1-Pentynyl)(2-tri-n-butylstannylvinyl)cuprate; 1-Pentynylcopper(I); 1-Pentynylcopper(I)-Hexamethylphosphorous Triamide.

1. Scott, W. J.; Crisp, G. T.; Stille, J. K. JACS 1984, 106, 4630.

Matthew E. Voss

The Du Pont Merck Pharmaceutical Company, Wilmington, DE, USA

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